Water → methyl (Z)-3-methoxy-2-(o-tolyl)prop-2-enoate

HRID 1613924Notes

Reaction equation

HRID 1613924 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[CH:13][OH:14])[C:9]([O:11][CH3:12])=[O:10].[H-].[Na+].[CH3:17]I.O>O1CCCC1>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1/[C:8](=[CH:13]/[O:14][CH3:17])/[C:9]([O:11][CH3:12])=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67027340Methyl 2-(2-methyl phenyl)-3-hydroxy-2-propenoate

Product 1

HCID 5478050methyl (Z)-3-methoxy-2-(o-tolyl)prop-2-enoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 44 g of the product of Step B in 400 ml of tetrahydrofuran was introduced at 20°-25° C. into a solution of 700 ml of tetrahydrofuran and 11 g of sodium hydride (50% in oil). The reaction mixture was stirred for one hour and 150 ml of methyl iodide were added. The mixture was stirred for 5 hours and poured into water. Extraction was carried out with methylene chloride and the extracts were dried and brought to dryness to obtain 47.2 g of product which was chromatographed on silica and eluted with hexane-ethyl acetate mixture (7-3) to obtain the following:

Workup

  1. stirringThe mixture was stirred for 5 hours
  2. extractionExtraction
  3. customthe extracts were dried

Sources & evidence

ORD record
ord-c716ff91c7fa4193919e68953307839a
Source dataset
uspto-grants-1993_03
Patent number
US05194622

Reaction notes

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